Cyclodehydration of N-(Aminoalkyl)benzamides under Mild Conditions with a Hendrickson Reagent Analogue

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• 作者：Wendy A. Loughlin ; Ian D. Jenkins ; Maria J. Petersson
• 刊名：The Journal of Organic Chemistry
• 出版年：2013
• 出版时间：July 19, 2013
• 年：2013
• 卷：78
• 期：14
• 页码：7356-7361
• 全文大小：296K
• 年卷期：v.78,no.14(July 19, 2013)
• ISSN：1520-6904

文摘

Methods for the cyclodehydration of N-(aminoalkyl)benzamides are few and employ harsh reaction conditions. We have found that the easily prepared phosphonium anhydrides 1 (Hendrickson reagent) or 2 can be used for cyclodehydration of N-(aminoalkyl)benzamides under very mild conditions (room temperature) to produce five-, six-, and seven-membered cyclic amidines. Good yields are obtained by employing a temporary trityl group protection strategy. Cyclic analogue 2 can be used when the product cyclic amidine is organic-soluble, thus producing water-soluble byproducts.